How To Wear Knee High Boots

Anthropologie Pilcro Tiered Corduroy Dress, Celine Medium Triomphe Belt, Vince Camuto Suede Boots
Shop the Dress | Belt | Similar Boots

If there’s one thing my closet is always filled to the brim with, it’s handbags and boots.

While I love all kinds of boots, there’s something incredibly timeless and classic about a knee-high boot. There’s something to be said about a shoe that can keep you both warm and stylish simultaneously. Knee-high boots are a perfect addition to any cold-weather ensemble, whether you rock these with dresses or skirts or layered over skinny jeans. I also love to pair my knee-high boots with warm-weather dresses to transition them into the new season.

Looking for some fall fashion inspo? Today, I’m sharing a round-up of ways to wear knee-high boots for different occasions.

How To Wear Knee-High Boots

How To Wear Knee High Boots: Schutz Abbey Boots
Shop the Coat | Top | Skirt | Similar Boots

Are Knee High Boots Still In Style?

Knee-high boots are making a huge comeback this season. Over-the-knee boots? For me, they feel a little dated, and I’ve been freeing the kneecaps this year. However, if you still want to rock your OTK boots, by all means — do what feels best for you!

In 2022, there are some key boot trends that you should keep an eye out for. These trends include:

  • Western Boots (AKA a modern take on the cowboy boot)
  • Pointed Toe Boots
  • Lug Sole Boots
  • Slouchy Boots
  • Stiletto Heels (but honestly, rock a boot with a chunky heel if you want!)

Knee-High Boots: Outfit Ideas

How To Wear Knee High Boots: Anthropologie Pilcro Tiered Corduroy Dress, Celine Medium Triomphe Belt, Vince Camuto Suede Boots

Suede Boots & A Mini Dress

One outfit combo I’ve been wearing on repeat is the suede boot + mini dress combo. This combo is ideal for the 65-ish degree day. When I went to New York last week, they were experiencing a bit of a heat wave, and this was one of the most comfortable outfit options I had for the unseasonably warm fall weather. These boots are older, but I love this updated suede boot with a pointed toe and a chunky heel.


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A post shared by Patricia | Peexo (@peexo)

Leather Boots & Shorts

Whether you live in a warm climate like I do or are experiencing an unseasonably warm fall, it might be time to pair your favorite pair of shorts with your fall boots. I love how Patricia paired her pointed-toe black leather boots with a pair of faux leather shorts — it’s chic, elevated, and very on-trend for 2022.


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A post shared by Thamarr (@musingsofacurvylady)

The Modern Go-Go Boot

Don’t shy away from a white boot this season. I absolutely adore the way that Thamarr styles these white knee-high boots — this look is retro-inspired perfection. By the way — her shoes also come in a regular and wide calf option. You can shop her exact look here.


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A post shared by Sarah Chiwaya – Plus Size Fashion in NYC (@curvily)

Knee-High Boots + A Midi Dress

I love wearing midi dresses year-round, and a great way to stay extra warm during colder months is to layer a pair of knee-high boots underneath your midi dresses. Sarah, who is pictured above, has styled this look flawlessly. The black boots paired with the bold purple coat and dress? Chef’s kiss! By the way, she also has an extensive guide to wide-calf boots on her blog!


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A post shared by Kaye Bassey | style & beauty (@kayebassey)

Skinny Jeans + Knee High Boots

Ah, skinny jeans. This might be the millennial in me speaking, but they’re extra practical for colder months because you can tuck them into your favorite knee-high boots. Don’t donate all of the pairs in your closet just yet!

Kaye has styled this casual look perfectly: this skinny jean ensemble is incredibly chic and modern.

The Best Knee High Boots

The Best Lug Sole Knee-High Boots

One essential knee-high boot trend for 2022? The lug sole. You can find a lug sole on a trusty riding boot or on shoes that are more Y2K inspired. Yes, my friends, that means if you held on to your riding boots from the 2010s, they’re back in style!


The Best Western Knee-High Boots

Listen: I’m all about the yee-haw agenda this season. Western boots are all the rage right now. A legit pair of cowboy boots can run you hundreds of dollars. However, these western-inspired knee-high boots won’t make as big of a dent in your wallet.


The Best Statement Knee-High Boots

Okay, so let’s be honest: how many pairs of black and brown boots do you own? Too many? I may or may not be in the same boat. There are only so many ways you can stretch a neutral boot!

If you want to switch things up this season, have fun with different colors, prints, and textures. I promise you won’t want to take these boots off!


The Best Wide-Calf Knee-High Boots

I love the look of a leather boot, but sometimes, leather doesn’t entirely mold to our legs as we want it to. Enter: the wide-calf boot. For those folks who are blessed with thicker legs, here are some wide calf boot options for you to enjoy!

As mentioned above, I still think Sarah from Curvily has the ultimate guide for wide-calf boots. Depending on the brand, I bounce in between a straight size and a wide calf size, so she’s more of an expert in this field!


The Best Narrow-Calf Knee-High Boots

If you’re on the other side of the spectrum and need a tighter fit, here are some of my top narrow-calf knee-high boot picks. Regardless, I would recommend always measuring your calf circumference before placing an order — some boots may be more accommodating to a narrow calf, even if they aren’t necessarily labeled as that type of boot. 


What’s your favorite knee-high boot trend this season? Let me know in the comments below!

Photos (of me!) by Tom McGovern

Leave a Comment


  1. Christine wrote:

    Very happy to see knee-high boots making a comeback!

    Posted 11.10.22 Reply